Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot sila-stetter/paal-knorr strategy

Ashwin R. Bharadwaj; Karl A. Scheidt

doi:10.1021/ol049044t

Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot sila-stetter/paal-knorr strategy

Ashwin R. Bharadwaj, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

206 Scopus citations

Abstract

(Equation Presented) A multicomponent synthesis of highly substituted pyrroles catalyzed by thiazolium salts has been disclosed. The reaction employs an acyl anion conjugate addition reaction of acylsilanes (sila-Stetter) and unsaturated ketones to generate 1,4-dicarbonyl compounds in situ. The subsequent addition of various amines promotes a Paal-Knorr reaction, affording the desired pyrrole nucleus in an efficient one-pot process.

Original language	English (US)
Pages (from-to)	2465-2468
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	14
DOIs	https://doi.org/10.1021/ol049044t
State	Published - Jul 8 2004

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Equation Presented) A multicomponent synthesis of highly substituted pyrroles catalyzed by thiazolium salts has been disclosed. The reaction employs an acyl anion conjugate addition reaction of acylsilanes (sila-Stetter) and unsaturated ketones to generate 1,4-dicarbonyl compounds in situ. The subsequent addition of various amines promotes a Paal-Knorr reaction, affording the desired pyrrole nucleus in an efficient one-pot process.",

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T1 - Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot sila-stetter/paal-knorr strategy

AU - Bharadwaj, Ashwin R.

AU - Scheidt, Karl A.

PY - 2004/7/8

Y1 - 2004/7/8

N2 - (Equation Presented) A multicomponent synthesis of highly substituted pyrroles catalyzed by thiazolium salts has been disclosed. The reaction employs an acyl anion conjugate addition reaction of acylsilanes (sila-Stetter) and unsaturated ketones to generate 1,4-dicarbonyl compounds in situ. The subsequent addition of various amines promotes a Paal-Knorr reaction, affording the desired pyrrole nucleus in an efficient one-pot process.

AB - (Equation Presented) A multicomponent synthesis of highly substituted pyrroles catalyzed by thiazolium salts has been disclosed. The reaction employs an acyl anion conjugate addition reaction of acylsilanes (sila-Stetter) and unsaturated ketones to generate 1,4-dicarbonyl compounds in situ. The subsequent addition of various amines promotes a Paal-Knorr reaction, affording the desired pyrrole nucleus in an efficient one-pot process.

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U2 - 10.1021/ol049044t

DO - 10.1021/ol049044t

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Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot sila-stetter/paal-knorr strategy

Abstract

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